EP1156042A1 - Process for the preparation of glycerol carbonate - Google Patents
Process for the preparation of glycerol carbonate Download PDFInfo
- Publication number
- EP1156042A1 EP1156042A1 EP00905322A EP00905322A EP1156042A1 EP 1156042 A1 EP1156042 A1 EP 1156042A1 EP 00905322 A EP00905322 A EP 00905322A EP 00905322 A EP00905322 A EP 00905322A EP 1156042 A1 EP1156042 A1 EP 1156042A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glycerol
- reaction
- process according
- conducted
- glycerol carbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 63
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004202 carbamide Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 5
- 229940095564 anhydrous calcium sulfate Drugs 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
Definitions
- the present invention relates to an inexpensive process for preparing glycerol carbonate.
- Glycerol carbonate is applied to use in various fields, e.g. raw materials for synthesis of polymers such as polyester, polycarbonate, polyurethane and polyamide, surfactants and lubricating oils.
- polymers such as polyester, polycarbonate, polyurethane and polyamide, surfactants and lubricating oils.
- German Patent No. 19756454 discloses application to an emulsifier for cosmetics and a lustering agent.
- US-A 2856413 it can be easily converted to glycidol.
- a reaction thereof with phosgene and an exchange reaction with a dialkyl carbonate are known as a conventional method of preparing glycerol carbonate from glycerol.
- a method of reacting glycerol with carbon monoxide and oxygen at a high pressure in the presence of a catalyst is also known in JP-A 6-157509, corresponding to US-A 5359094.
- JP-A 6-157509 A less expensive, simpler method using a highly safe material, however, has been desired. It has been therefore asked to conduct the reaction with a catalyst easily treated or without catalyst.
- the purpose of the present invention is to provide a process for preparing glycerol carbonate simply at a low cost.
- glycerol carbonate can be synthesized by reaction of glycerol with urea.
- the present invention provides a process for preparing glycerol carbonate by reaction of glycerol with urea.
- the invention provides a process for preparing glycerol carbonate, comprising reacting glycerol with urea in the presence of a metal oxide catalyst or in the absence of any catalyst.
- the reaction is preferably carried out in the presence of a dehydrating agent.
- the reaction may be preferably carried out in the presence of anhydrous magnesium sulfate, anhydrous sodium sulfate, anhydrous calcium sulfate or a molecular sieve.
- the catalyst is desirably used in an amount of 0.001 to 10 wt % based on glycerol.
- the reaction is preferably conducted at a temperature between 100°C and 140°C, more preferably at a temperature between 100°C and 120°C, in particular preferably at a temperature between 110°C and 120°C.
- glycerol and urea are used as starting materials.
- Glycerol carbonate can be easily produced just by reacting them with each other.
- the feeding mole ratio of urea to glycerol may be preferably 0.2 to 2.0, particularly 0.5 to 1.0.
- the invention reaction does not essentially need a catalyst.
- the reaction proceeds smoothly by using as catalyst a metal oxide such as zinc oxide and an alkaline earth metal oxide, e.g. magnesium oxide.
- a preferred amount of the used catalyst is 0.001 to 10 wt % based on glycerol.
- a sufficiently dehydrated glycerol In the present process, it is desirable to use a sufficiently dehydrated glycerol.
- dehydrating agents such as anhydrous magnesium sulfate, anhydrous calcium sulfate, anhydrous sodium sulfate and molecular sieve may be preferably used.
- the reaction may be conducted preferably in passing of nitrogen gas or at a reduced pressure in order to remove out generated ammmonia efficiently.
- the passing amount of nitrogen gas is not specified as long as ammonia and excess water can be removed.
- Nitrogen gas may be preferably introduced into the glycerol liquid phase.
- the reaction may be conducted at a reduced pressure, for example, in the range of 13.3 to 101 kPa.
- a preferred reaction temperature ranges from 80° to 160°C, more preferably from 100 to 140°C and particularly preferably from 110 to 120°C.
- Glycerol carbonate can be prepared simply. Glycerol carbonate obtained by the present process can be easily converted to glycidol by known means.
- glycerol 92 g was fed in a flask. It was heated up to 120°C in passing of nitrogen gas and then was stirred for two hours. It was cooled down to 80°C. Then 60 g of urea was dissolved therein and 10 g of anhydrous magnesium sulfate was added thereto. The mixture was heated up to 120° to 140°C and allowed to stand as it was for reaction over 6 hours. It was found in gas chromatographic analysis that a glycerol conversion was 72 % and a selectivity of glycerol carbonate was 92 %.
- glycerol 92 g was fed in a flask. It was heated up to 120°C in passing of nitrogen gas and then was stirred for two hours. It was cooled down to 80°C. Then 60 g of urea was dissolved therein and 7.0 g of zinc oxide was added thereto. The mixture was heated up to 120°C and allowed to stand as it was for reaction over 6 hours. It was found in gas chromatographic analysis that a glycerol conversion was 62 % and a selectivity of glycerol carbonate was 93 %.
- Example 1 100 g of glycerol carbonate obtained in Example 1 was fed in a flask. 10 g of sodium sulfate was added thereto. The mixture was heated up to 200 to 210°C at the reduced pressure of 3.33 kPa, while stirred. In the meanwhile glycidol being produced together with carbon dioxide was recovered in the form of 53.5 g of the distillate (approximate yield 85 %). In gas chromatographic analysis the glycidol was found to have a purity of 90 % and contain 10 % of glycerol carbonate being the starting material. The selectivity of glycidol was 99 % or higher.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention provides a simple and
inexpensive process for preparing glycerol carbonate.
Namely, according to the present invention, glycerol
carbonate is prepared by reacting glycerol with urea.
Description
The present invention relates to an inexpensive
process for preparing glycerol carbonate.
Glycerol carbonate is applied to use in various
fields, e.g. raw materials for synthesis of polymers such
as polyester, polycarbonate, polyurethane and polyamide,
surfactants and lubricating oils. For example, German
Patent No. 19756454 discloses application to an emulsifier
for cosmetics and a lustering agent. Furthermore it is
shown in US-A 2856413 that it can be easily converted to
glycidol.
A reaction thereof with phosgene and an exchange
reaction with a dialkyl carbonate are known as a
conventional method of preparing glycerol carbonate from
glycerol. A method of reacting glycerol with carbon
monoxide and oxygen at a high pressure in the presence of a
catalyst is also known in JP-A 6-157509, corresponding to
US-A 5359094. A less expensive, simpler method using a
highly safe material, however, has been desired. It has
been therefore asked to conduct the reaction with a
catalyst easily treated or without catalyst.
The purpose of the present invention is to provide a
process for preparing glycerol carbonate simply at a low
cost.
The present inventors have found that glycerol
carbonate can be synthesized by reaction of glycerol with
urea.
The present invention provides a process for preparing
glycerol carbonate by reaction of glycerol with urea.
More specifically, the invention provides a process
for preparing glycerol carbonate, comprising reacting
glycerol with urea in the presence of a metal oxide
catalyst or in the absence of any catalyst.
The reaction is preferably carried out in the presence
of a dehydrating agent.
It is preferable to feed urea in a 0.2 to 2.0 times as
many moles as glycerol.
The reaction may be preferably carried out in the
presence of anhydrous magnesium sulfate, anhydrous sodium
sulfate, anhydrous calcium sulfate or a molecular sieve.
The catalyst is desirably used in an amount of 0.001
to 10 wt % based on glycerol.
The reaction is preferably conducted at a temperature
between 100°C and 140°C, more preferably at a temperature
between 100°C and 120°C, in particular preferably at a
temperature between 110°C and 120°C.
In the present process comparatively inexpensive
glycerol and urea are used as starting materials. Glycerol
carbonate can be easily produced just by reacting them with
each other. The feeding mole ratio of urea to glycerol may
be preferably 0.2 to 2.0, particularly 0.5 to 1.0.
The invention reaction does not essentially need a
catalyst. The reaction proceeds smoothly by using as
catalyst a metal oxide such as zinc oxide and an alkaline
earth metal oxide, e.g. magnesium oxide. A preferred
amount of the used catalyst is 0.001 to 10 wt % based on
glycerol.
In the present process, it is desirable to use a
sufficiently dehydrated glycerol. In the reaction
dehydrating agents such as anhydrous magnesium sulfate,
anhydrous calcium sulfate, anhydrous sodium sulfate and
molecular sieve may be preferably used. The reaction may
be conducted preferably in passing of nitrogen gas or at a
reduced pressure in order to remove out generated ammmonia
efficiently. The passing amount of nitrogen gas is not
specified as long as ammonia and excess water can be
removed. Nitrogen gas may be preferably introduced into
the glycerol liquid phase. The reaction may be conducted
at a reduced pressure, for example, in the range of 13.3 to
101 kPa.
A preferred reaction temperature ranges from 80° to
160°C, more preferably from 100 to 140°C and particularly
preferably from 110 to 120°C.
According to the present process, comparatively
inexpensive materials can be used. No high pressure
equipment is not required. Glycerol carbonate can be
prepared simply. Glycerol carbonate obtained by the
present process can be easily converted to glycidol by
known means.
92 g of glycerol was fed in a flask. It was heated up
to 120°C in passing of nitrogen gas and then was stirred
for two hours. It was cooled down to 80°C. Then 60 g of
urea was dissolved therein and 10 g of anhydrous magnesium
sulfate was added thereto. The mixture was heated up to
120° to 140°C and allowed to stand as it was for reaction
over 6 hours. It was found in gas chromatographic analysis
that a glycerol conversion was 72 % and a selectivity of
glycerol carbonate was 92 %.
92 g of glycerol was fed in a flask. It was heated up
to 120°C in passing of nitrogen gas and then was stirred
for two hours. It was cooled down to 80°C. Then 60 g of
urea was dissolved therein and 7.0 g of zinc oxide was
added thereto. The mixture was heated up to 120°C and
allowed to stand as it was for reaction over 6 hours. It
was found in gas chromatographic analysis that a glycerol
conversion was 62 % and a selectivity of glycerol carbonate
was 93 %.
92 g of glycerol and 7.0 g of anhydrous magnesium
sulfate were introduced into a flask. They were heated up
to 120°C in passing of nitrogen gas and stirred for two
hours. They were cooled down to 80°C. Then 60 g of urea
was dissolved therein and 7.0 g of zinc oxide was added
thereto. The mixture was gradually heated to 120°C and
allowed to stand as it was for reaction over 6 hours. It
was found in gas chromatographic analysis that a glycerol
conversion was 64 % and a selectivity of glycerol carbonate
was 92 %.
100 g of glycerol carbonate obtained in Example 1 was
fed in a flask. 10 g of sodium sulfate was added thereto.
The mixture was heated up to 200 to 210°C at the reduced
pressure of 3.33 kPa, while stirred. In the meanwhile
glycidol being produced together with carbon dioxide was
recovered in the form of 53.5 g of the distillate
(approximate yield 85 %). In gas chromatographic analysis
the glycidol was found to have a purity of 90 % and contain
10 % of glycerol carbonate being the starting material.
The selectivity of glycidol was 99 % or higher.
Claims (8)
- A process for preparing glycerol carbonate, which comprises reacting glycerol with urea in the presence of a metal oxide catalyst or in the absence of catalyst.
- The process according to Claim 1, wherein the reaction is conducted in the presence of a dehydrating agent.
- The process according to Claim 1, wherein urea is fed in an amount of 0.2 to 2.0 times as many moles as glycerol.
- The process according to Claim 1, wherein the reaction is conducted in the presence of anhydrous magnesium sulfate, anhydrous calcium sulfate, anhydrous sodium sulfate or molecular sieve as the dehydrating agent.
- The process according to Claim 1, wherein the catalyst is used in an amount of 0.001 to 10 % by weight to glycerol.
- The process according to Claim 1 or 2, wherein the reaction is conducted at a temperature between 100°C and 140°C.
- The process according to Claim 1 or 2, wherein the reaction is conducted at a temperature between 100°C and 120°C.
- The process according to Claim 1 or 2, wherein the reaction is conducted at a temperature between 110°C and 120°C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4610399 | 1999-02-24 | ||
| JP04610399A JP3905242B2 (en) | 1999-02-24 | 1999-02-24 | Method for producing glycerin carbonate |
| PCT/JP2000/001072 WO2000050415A1 (en) | 1999-02-24 | 2000-02-24 | Process for the preparation of glycerol carbonate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP1156042A1 true EP1156042A1 (en) | 2001-11-21 |
| EP1156042A4 EP1156042A4 (en) | 2002-07-03 |
| EP1156042B1 EP1156042B1 (en) | 2005-04-20 |
Family
ID=12737670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00905322A Expired - Lifetime EP1156042B1 (en) | 1999-02-24 | 2000-02-24 | Process for the preparation of glycerol carbonate |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6495703B1 (en) |
| EP (1) | EP1156042B1 (en) |
| JP (1) | JP3905242B2 (en) |
| DE (1) | DE60019561T2 (en) |
| WO (1) | WO2000050415A1 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2174937A1 (en) | 2008-10-08 | 2010-04-14 | Arkema France | Synthesis process of polyol carbonate from polyols, conducted in using a solvent selective for polyols carbonates |
| WO2010043581A1 (en) * | 2008-10-17 | 2010-04-22 | Basf Se | Method and catalysts for producing cyclic carbonates |
| EP2028181A4 (en) * | 2006-06-15 | 2011-01-26 | Kao Corp | Process for production of glycidol |
| CN102464646A (en) * | 2010-11-16 | 2012-05-23 | 中国科学院兰州化学物理研究所 | A kind of synthetic method of glycerol carbonate |
| FR2970254A1 (en) * | 2011-01-11 | 2012-07-13 | Rhodia Operations | PROCESS FOR THE PREPARATION OF ALCOHOL CARBONATE |
| WO2013074155A1 (en) | 2011-11-15 | 2013-05-23 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
| EP2873661A1 (en) | 2013-11-14 | 2015-05-20 | Arkema France | Synthesis process of trimethylene carbonate from 1,3-propanediol and urea by heterogeneous catalysis |
| KR20160084738A (en) | 2015-01-06 | 2016-07-14 | 부산대학교 산학협력단 | Method for preparation of glycerol carbonate by using ZIF-95 as catalyst |
| EP3401350A1 (en) | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| EP3401348A1 (en) | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| EP3670618A1 (en) | 2018-12-20 | 2020-06-24 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| WO2022200247A1 (en) | 2021-03-22 | 2022-09-29 | Bracco Imaging Spa | Industrial synthesis of serinol |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4732058B2 (en) * | 2005-08-01 | 2011-07-27 | 花王株式会社 | Method for producing glycerin carbonate |
| GB0709460D0 (en) | 2007-05-17 | 2007-06-27 | Croda Int Plc | Method of making polyglycerol esters |
| JP2008285457A (en) * | 2007-05-21 | 2008-11-27 | Kao Corp | Method for producing glycerin carbonate |
| JP5250225B2 (en) * | 2007-08-28 | 2013-07-31 | 花王株式会社 | Method for producing glycerin carbonate |
| JP5188126B2 (en) * | 2007-09-11 | 2013-04-24 | 花王株式会社 | Method for producing glycerin carbonate |
| JP5386146B2 (en) * | 2007-11-15 | 2014-01-15 | 花王株式会社 | Method for producing glycidol |
| JP2009149576A (en) * | 2007-12-21 | 2009-07-09 | Kao Corp | Method for producing glycidol |
| GB0903233D0 (en) | 2009-02-25 | 2009-04-08 | Univ Cardiff | Method for making organic carbonates and sulphur analogues |
| CN101811971B (en) * | 2010-04-23 | 2012-11-21 | 浙江华诺化工有限公司 | Preparation method of glycerol carbonate |
| KR101307559B1 (en) * | 2011-04-06 | 2013-09-12 | 한국과학기술연구원 | Synthesis of glycerol carbonate using high active catalysts |
| KR101316608B1 (en) * | 2011-04-15 | 2013-10-15 | 한국과학기술연구원 | Method for preparing glycerol carbonate using Zn catalysts and acid |
| KR101425985B1 (en) * | 2012-04-10 | 2014-08-14 | 한국생산기술연구원 | A catalyst for preparing glycerol carbonate from glycerol, a preparation method thereof, and a preparation method of glycerol carbonate from glycerol by using the catalyst |
| US11578034B2 (en) | 2017-04-11 | 2023-02-14 | Sabic Global Technologies B.V. | Integrated process for production of glycerol carbonate (4-hydroxymethyl-2-oxo-1, 3-dioxolane) and urea |
| CN114315762A (en) * | 2020-09-29 | 2022-04-12 | 上海抚佳精细化工有限公司 | A kind of method for continuous production of glycidol |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60100571A (en) * | 1983-11-06 | 1985-06-04 | Kyoto Yakuhin Kogyo Kk | Dioxole derivative |
| US5003084A (en) | 1990-02-20 | 1991-03-26 | Texaco Chemical Company | Process for preparing alkylene carbonates |
| DE69328056T2 (en) * | 1992-07-31 | 2000-10-05 | Mitsubishi Gas Chemical Co., Inc. | Process for the production of alkylene carbonates |
| DE4225870A1 (en) | 1992-08-05 | 1994-02-10 | Basf Ag | Process for the preparation of glycerol carbonate |
| FR2733232B1 (en) * | 1995-04-24 | 1997-06-13 | Organisation Nationale Interpr | PROCESS FOR THE MANUFACTURE OF GLYCEROL CARBONATE FROM GLYCEROL AND AN ORGANIC CYCLIC CARBONATE, IN PARTICULAR ETHYLENE OR PROPYLENE CARBONATE |
| FR2778182B1 (en) * | 1998-04-30 | 2000-07-21 | Organisation Nationale Interpr | PROCESS FOR THE MANUFACTURE OF GLYCEROL CARBONATE |
-
1999
- 1999-02-24 JP JP04610399A patent/JP3905242B2/en not_active Expired - Fee Related
-
2000
- 2000-02-24 EP EP00905322A patent/EP1156042B1/en not_active Expired - Lifetime
- 2000-02-24 WO PCT/JP2000/001072 patent/WO2000050415A1/en not_active Ceased
- 2000-02-24 US US09/913,719 patent/US6495703B1/en not_active Expired - Fee Related
- 2000-02-24 DE DE60019561T patent/DE60019561T2/en not_active Expired - Fee Related
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2028181A4 (en) * | 2006-06-15 | 2011-01-26 | Kao Corp | Process for production of glycidol |
| US7888517B2 (en) | 2006-06-15 | 2011-02-15 | Kao Corporation | Process for production of glycidol |
| EP2174937A1 (en) | 2008-10-08 | 2010-04-14 | Arkema France | Synthesis process of polyol carbonate from polyols, conducted in using a solvent selective for polyols carbonates |
| WO2010043581A1 (en) * | 2008-10-17 | 2010-04-22 | Basf Se | Method and catalysts for producing cyclic carbonates |
| CN102464646A (en) * | 2010-11-16 | 2012-05-23 | 中国科学院兰州化学物理研究所 | A kind of synthetic method of glycerol carbonate |
| US9238638B2 (en) | 2011-01-11 | 2016-01-19 | Rhodia Operations | Method for preparing alcohol carbonate using rare earth oxides as catalysts |
| WO2012095435A1 (en) * | 2011-01-11 | 2012-07-19 | Rhodia Operations | Method for preparing alcohol carbonate using rare earth oxides as catalysts |
| FR2970254A1 (en) * | 2011-01-11 | 2012-07-13 | Rhodia Operations | PROCESS FOR THE PREPARATION OF ALCOHOL CARBONATE |
| WO2013074155A1 (en) | 2011-11-15 | 2013-05-23 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
| US8703679B2 (en) | 2011-11-15 | 2014-04-22 | Yue-Rong Li | Glycerol-containing functional fluid |
| EP2873661A1 (en) | 2013-11-14 | 2015-05-20 | Arkema France | Synthesis process of trimethylene carbonate from 1,3-propanediol and urea by heterogeneous catalysis |
| KR20160084738A (en) | 2015-01-06 | 2016-07-14 | 부산대학교 산학협력단 | Method for preparation of glycerol carbonate by using ZIF-95 as catalyst |
| EP3401350A1 (en) | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| EP3401348A1 (en) | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| WO2018206181A1 (en) | 2017-05-11 | 2018-11-15 | Henkel Ag & Co. Kgaa | Method for producing functionalized polyesters |
| WO2018206362A1 (en) | 2017-05-11 | 2018-11-15 | Henkel Ag & Co. Kgaa | Method for producing functionalized polyesters |
| US11161935B2 (en) | 2017-05-11 | 2021-11-02 | Henkel Ag & Co. Kgaa | Method for producing functionalized polyesters |
| EP3670618A1 (en) | 2018-12-20 | 2020-06-24 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| WO2020126544A1 (en) | 2018-12-20 | 2020-06-25 | Henkel Ag & Co. Kgaa | Method for producing functionalized polyesters |
| US12122871B2 (en) | 2018-12-20 | 2024-10-22 | Henkel Ag & Co. Kgaa | Method for producing functionalized polyesters |
| WO2022200247A1 (en) | 2021-03-22 | 2022-09-29 | Bracco Imaging Spa | Industrial synthesis of serinol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60019561T2 (en) | 2006-02-23 |
| JP3905242B2 (en) | 2007-04-18 |
| EP1156042B1 (en) | 2005-04-20 |
| JP2000247967A (en) | 2000-09-12 |
| WO2000050415A1 (en) | 2000-08-31 |
| DE60019561D1 (en) | 2005-05-25 |
| US6495703B1 (en) | 2002-12-17 |
| EP1156042A4 (en) | 2002-07-03 |
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